Three-Component Domino Knoevenagel/Hetero-Diels-Alder Reaction for the Synthesis of the Amino Sugars 2-Acetoxyforosamine and 2-Acetoxyossamine - Experimental and Theoretical Results

The three‐component domino Knoevenagel/hetero‐Diels–Alder reaction of nitroacetone (6), formaldehyde and ethoxyvinylacetate (4) leads to dihydropyrans 10 and 11, which after hydrogenation of the double bond as well as consecutive reduction of the nitro group and reductive amination give the desired...

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Veröffentlicht in:	European Journal of Organic Chemistry 2011-11, Vol.2011 (32), p.6574-6580
Hauptverfasser:	Tietze, Lutz F., Dietz, Simone, Böhnke, Niels, Düfert, M. Alexander, Objartel, Ina, Stalke, Dietmar
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Cycloaddition Domino reactions Exact sciences and technology Glycosides Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Kinetics and mechanisms Multicomponent reactions Organic chemistry Preparations and properties Reaction mechanisms Reactivity and mechanisms
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Zusammenfassung:	The three‐component domino Knoevenagel/hetero‐Diels–Alder reaction of nitroacetone (6), formaldehyde and ethoxyvinylacetate (4) leads to dihydropyrans 10 and 11, which after hydrogenation of the double bond as well as consecutive reduction of the nitro group and reductive amination give the desired forosamine‐type 2‐acetoxyamino sugars 21–24 and ossamine‐type 25. The three‐step synthesis of deoxyaminosugars by a three‐component dominoKnoevenagel/hetero‐Diels–Alder reaction starting from easily accessible substrates is reported.
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.201100725